1-[(Benzylamino)methyl]cyclohexan-1-OL → N4-benzyl-N4-[(1-hydroxycyclohexyl)methyl]-N1-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(4-thiazolylmethyl)butanediamide

HRID 742832Notes

Reaction equation

[CH:1]1([CH2:7][C@H:8]([NH:17][C:18](=[O:30])[C@H:19]([CH2:24][C:25]2[N:26]=[CH:27][S:28][CH:29]=2)[CH2:20][C:21](O)=[O:22])[C@@H:9]([OH:16])[C@@H:10]([OH:15])[CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:31]1([CH2:37][NH:38][CH2:39][C:40]2([OH:46])[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[CH2:37]([N:38]([CH2:39][C:40]1([OH:46])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]1)[C:21](=[O:22])[CH2:20][C@@H:19]([CH2:24][C:25]1[N:26]=[CH:27][S:28][CH:29]=1)[C:18]([NH:17][C@@H:8]([CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C@@H:9]([OH:16])[C@@H:10]([OH:15])[CH2:11][CH:12]([CH3:13])[CH3:14])=[O:30])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

Reactant 2

HCID 194176781-[(Benzylamino)methyl]cyclohexan-1-OL

HCID 228615624-{[1(S)-(Cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]amino}-4-oxo-3(R)-(4-thiazolylmethyl)butanoic Acid

Product 1

HCID 15340931N4-benzyl-N4-[(1-hydroxycyclohexyl)methyl]-N1-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(4-thiazolylmethyl)butanediamideYield 45.6%

Procedure

4{[1(S)-(Cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]amino}-4-oxo-3(R)-(4-thiazolylmethyl)-butanoic acid (61 mg, 0.14 mmol, described in example 2, section D) was coupled with 1-{[(phenylmethyl)amino]methyl}cyclohexanol (31 mg, 0.14 mmol, described in example 1, section D) according to the procedure described in example 3 to give the title compound (41 mg, 17%); 1H NMR (400 MHz, DMSO-d6) (2.2:1 mixture of rotamers) δ9.00 and 8.95 (d, J=1.8 Hz, 1H), 7.76 and 7.71 (d, J=8.9 Hz, 1H), 7.36-7.20 (m,4H), 7.15 and 7.10 (d, J=7.2 Hz,2H), 4.77 (broad s,2H), 4.62-4.58 (m,2H), 4.43 and 4.34 (s,1H), 4.13-4.02 (m,1H), 3.17 (d, J=13.8 Hz, 1H), 3.09-2.76 (m,5H), 2.62 (dd, J1 =8.1 Hz, J2 =16.5 Hz, 1H), 2.32 (dd, J1 =5.4 Hz, J2 2 =16.1 Hz, 1H), 1.68-1.25 (m,21H), 1.22-1.03 (m,6H), 0.85 and 0.84 (d, J=6.6 Hz, 3H), 0.73 (t, J=5.4 Hz,3H); FAB mass spectrum , m/z: 642 (M+H)+.

Sources & evidence

ORD record: ord-6f52e6ddbed64df0886e36b3f71a497f
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05554634

Reaction notes

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